HCID 67923156, compound → HCID 15036643, compound

HRID 1087015Notes

Reaction equation

HRID 1087015 reaction equation
[CH:1]1([CH:7]=[CH:8][C:9]2[CH:27]=[CH:26][C:12]([CH2:13][CH2:14][N:15]3[C:19](=[O:20])[C:18]4=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]4[C:16]3=[O:25])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>[Pd].C(OCC)(=O)C>[CH:1]1([CH2:7][CH2:8][C:9]2[CH:27]=[CH:26][C:12]([CH2:13][CH2:14][N:15]3[C:16](=[O:25])[C:17]4=[CH:24][CH:23]=[CH:22][CH:21]=[C:18]4[C:19]3=[O:20])=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 67923156HCID 67923156, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15036643HCID 15036643, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The intermediate from Example 16, N-(p-cyclohexylvinylphenethyl)phthalimide (9.0 g) and 10% palladium on charcoal (0.9 g) in ethyl acetate (700 ml) is shaken with hydrogen at 3 atmospheres pressure over 7 hours. The mixture is filtered and the filtrate concentrated to dryness at reduced pressure to give N-[p-(2-cyclohexylethyl]-phenethyl]-phthalimide, m.p. 135°-138° after recrystallization from ethanol. The phthalimide (5.75 g) is added to a mixture of hydrazine hydrate (1.6 g) in methanol (100 ml) and heated under reflux for 18 hours. The mixture is concentrated to dryness at reduced pressure, made basic with cold concentrated aqueous potassium hydroxide and extracted with ethyl acetate. The organic extract is washed with water, then brine, dried over sodium sulphate and concentrated to dryness at reduced pressure to give the desired amine as an oil which gradually solidifies on standing.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate concentrated to dryness at reduced pressure

Sources & evidence

ORD record
ord-90a0248dff3940a3af246f4158756ac0
Source dataset
uspto-grants-1991_07
Patent number
US05034381

Reaction notes

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